Abstract

The reaction of alkyl phenyl sulfones ( 1) with an excess of lithium powder and a catalytic amount of naphthalene (8 mol %) in the presence of a carbonyl compound or chlorotrimethylsilane (Barbier-type conditions) in THF at temperatures ranging between −78 and 20°C leads, after hydrolysis, to the expected products ( 2) arising from the corresponding alkyllithium generated in situ. When the same methodology is applied to sulfolene ( 3) or different alkyl phenyl sulfoxides ( 6), cyclic sulfinates 5 or products 2 are, respectively, obtained, the yields being, in general modest.

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